493-05-0Relevant articles and documents
Target directed enediyne prodrugs: hER and AhR degradation by a synthetic oxo-enediyne
Jones, Graham B.,Kilgore, Michael W.,Pollenz, Richard S.,Li, Aiwen,Mathews, Jude E.,Wright, Justin M.,Huber, Robert S.,Tate, Patricia L.,Price, Thomas L.,Sticca, Robert P.
, p. 1971 - 1976 (1996)
An efficient route to oxo-enediynes is presented. A simple oxo-enediyne has been synthesized, which cyclizes to give an isochroman. The agent shows cytotoxicity for ER rich breast cancer cells and a model for its mode of action is proposed.
Iron-catalyzed direct C(sp3)-H amination reactions of isochroman derivatives with primary arylamines under mild conditions
Chen, Di,Pan, Fuyou,Gao, Jianrong,Yang, Jianguo
, p. 2085 - 2088 (2013)
A direct C(sp3)-H amination reaction of isochroman derivatives with arylamines was developed in the presence of iron(II) salt. A variety of isochroman derivatives and primary amines were selectively transformed into the corresponding oxidative coupling products in good to excellent yield under mild conditions. Georg Thieme Verlag Stuttgart, New York.
Iridium-Catalyzed Enantioselective Hydrogenation of Oxocarbenium Ions: A Case of Ionic Hydrogenation
Lin, Zhenyang,Sun, Yongjie,Wang, Heng,Wen, Jialin,Yang, Tilong,Zhang, Xumu
, p. 6108 - 6114 (2020/03/04)
Ionic hydrogenation has not been extensively explored, but is advantageous for challenging substrates such as unsaturated intermediates. Reported here is an iridium-catalyzed hydrogenation of oxocarbenium ions to afford chiral isochromans with high enantioselectivities. A variety of functionalities are compatible with this catalytic system. In the presence of a catalytic amount of the Br?nsted acid HCl, an α-chloroether is generated in situ and subsequentially reduced. Kinetic studies suggest first-order kinetics in the substrate and half-order kinetics in the catalyst. A positive nonlinear effect, together with the half kinetic order, revealed a dimerization of the catalyst. Possible reaction pathways based on the monomeric iridium catalyst were proposed and DFT computational studies revealed an ionic hydrogenation pathway. Chloride abstraction and the cleavage of dihydrogen occur in the same step.
Ytterbium-Catalyzed Intramolecular [3 + 2] Cycloaddition based on Furan Dearomatization to Construct Fused Triazoles
Xu, Xiaoming,Zhong, Ying,Xing, Qingzhao,Gao, Ziwei,Gou, Jing,Yu, Binxun
, p. 5176 - 5181 (2020/07/14)
The 1,2,3-triazole-containing polycyclic architecture widely exists in a broad spectrum of synthetic bioactive molecules, and the development of expeditious methods to synthesize these skeletons remains a challenging task. In this work, the catalytic cyclization of biomass-derived 2-furylcarbinols with an azide to form fused triazoles is described. This approach takes advantage of a single catalyst Yb(OTf)3 and operates via a furfuryl-cation-induced intramolecular [3 + 2] cycloaddition/furan ring-opening cascade.
Enantioselective synthesis of tetrahydroisoquinoline derivatives via chiral-at-metal rhodium complex catalyzed [3+2] cycloaddition
Qurban, Saira,Du, Yu,Gong, Jun,Lin, Shao-Xia,Kang, Qiang
, p. 249 - 252 (2019/01/04)
An asymmetric [3+2] cycloaddition of C,N-cyclic azomethine imines with α,β-unsaturated 2-acyl imidazoles catalyzed by a chiral-at-metal rhodium complex has been developed. The corresponding C-1-substituted tetrahydroisoquinoline derivatives were obtained in high yields (>90%) with excellent stereoselectivities (up to 99% ee and >20?:?1 dr). The reaction can be conducted on a gram-scale using a low catalyst loading (0.5 mol%) with high yield and selectivity.
A rhodium-catalysed three-component reaction to access C1-substituted tetrahydroisoquinolines
Zhang, Dan,Liu, Junwen,Kang, Zhenghui,Qiu, Huang,Hu, Wenhao
, p. 9844 - 9848 (2019/12/05)
A rhodium-catalyzed three-component reaction of diazo compounds, anilines and C,N-cyclic azomethine imines via trapping of transient ammonium ylides was developed. This reaction provided a simple and convenient approach for the synthesis of pharmaceutically intriguing tetrahydroisoquinoline derivatives in moderate to good yields (36-85%) with good diastereoselectivities (up to 95 : 5 dr) under mild reaction conditions.
Synthesis of Tetrahydroisoquinolines through an Iron-Catalyzed Cascade: Tandem Alcohol Substitution and Hydroamination
Marcyk, Paul T.,Cook, Silas P.
, p. 6741 - 6744 (2019/09/07)
Rapid assembly of saturated nitrogen heterocycles - the synthetically more challenging variants of their aromatic relatives - can expedite the synthesis of biologically relevant molecules. Starting from a benzylic alcohol tethered to an unactivated alkene, an iron-catalyzed tandem alcohol substitution and hydroamination provides access to tetrahydroisoquinolines in a single synthetic step. Using a mild iron-based catalyst, the combination of these operations forms two carbon-nitrogen bonds and provides a unique annulation strategy to access this valuable core.
Cyclic ether synthesis from diols using trimethyl phosphate
Asai, Shota,Kato, Maho,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 4787 - 4790 (2017/07/06)
Cyclic ethers have been effectively synthesized via the intramolecular cyclization of diols using trimethyl phosphate and NaH. The present cyclization could proceed at room temperature to produce 5-7 membered cyclic ethers in good to excellent yields. Substrates possessing a chiral secondary hydroxy group were transformed into the corresponding chiral cyclic ethers along with the retention of their stereochemistries.
Synthesis of 5,6-Dihydropyrazolo[5,1-a]isoquinoline and Ethyl (Z)-3-Acetoxy-3-tosylpent-4-enoate through Tertiary-Amine-Catalyzed [3+2] Annulation
Lei, Yu,Xing, Jiao-Jiao,Xu, Qin,Shi, Min
, p. 3486 - 3490 (2016/07/28)
The 1,4-diazabicyclo[2.2.2]octane (DABCO) catalyzed divergent [3+2] annulation of C,N-cyclic azomethine imines with δ-acetoxyallenoates was developed; 5,6-dihydropyrazolo[5,1-a]isoquinolines and ethyl (Z)-3-acetoxy-3-tosylpent-4-enoates were afforded in moderate to good yields in a one-pot manner under mild conditions. This annulation reaction provides a highly efficient method to construct dinitrogen-fused heterocycles and ethyl (Z)-3-acetoxy-3-tosylpent-4-enoates at the same time.
Phosphane-Catalyzed [3+3] Annulation of C,N-Cyclic Azomethine Imines with Ynones: A Practical Method for Tricyclic Dinitrogen-Fused Heterocycles
Li, Zhen,Yu, Hao,Liu, Yang,Zhou, Leijie,Sun, Zhanhu,Guo, Hongchao
, p. 1880 - 1885 (2016/07/06)
A phosphane-catalyzed [3+3] annulation of azomethine imines with ynones has been developed. Under mild reaction conditions, the reaction proceeds smoothly to afford tricyclic dinitrogen-fused heterocyclic compounds in moderate to excellent yields with moderate to excellent stereoselectivies. Using a chiral phosphine as the catalyst, the reaction could work to give the cycloadduct in moderate yield with moderate enantioselectivity. (Figure presented.) .
